If you’re in the enterprise software / SaaS business, then you know that the sales process almost always includes a conversation with the CIO. This is a conversation you want to nail for obvious reasons.

Pitching to CIOs has its nuances, as I was reminded during two recent CIO events, a series that I host every few months.

Guests at these events comprise large enterprise CIOs, as well as founders of enterprise software and SaaS companies. The CIO attendees are a combination of IDG Venture’s CIO Advisory Board and selected senior IT executives from prominent enterprises. The startup attendees are from IDG’s portfolio companies, and more so, the founders of other interesting startups. Founders have the opportunity to present their solutions to the CIO audience. These events are relatively small by design, in order to foster intimate conversations and candid feedback.

At the last two events we were fortunate to have the CIOs of Hewlett-Packard, Akamai, Johnson & Johnson, Vertex, IHS, Credit Suisse, Gartner Group, Visioneer, Vail Resorts, CBS Interactive, as well as senior technologists from Google, KAR Auction Services, IDG, and Sears.

While we know these intuitively, the specifics are interesting. Some are reminders of what we already know, while others may be surprising and hold new insights.

1. Know your audience

Do your homework. Surprisingly, not everyone does basic preparation for meetings. Knowing your audience and personalizing your message even a little bit can be the difference between creating a real connection and talking into a vacuum.

If you are presenting to a small group, get the group involved. Ask for feedback and advice. If you are in a meeting with smart people, particularly ones who control billions of dollars of IT spend, you can glean great insight by listening.

Some CIOs are very technical, others are great business leaders. Remember CIOs differ from CTOs. Focus as much on the business case as the technology merits.

2. Have a great elevator pitch

Make sure you have a clear, succinct answer to “what exactly does your company do?” It is not a rhetorical question.

It is remarkable how dominant Google, Facebook, Twitter, Pinterest, LinkedIn are in creating ecosystems, and how dependent multiple startups are (particularly in social enterprise) on the “rules of engagement” in those ecosystems. Make sure you have a good answer to “what happens if Google changes its algorithm again” or “What if FB blocks you?”

According to many CIOs, it is hard to justify internal productivity applications. That’s table stakes these days.

CIOs really care about your backup, redundancy, security, and SLAs as much as what the product does.

Do not underestimate inertia, or how entrenched incumbents are in large companies.

Have a good answer to “why can’t we just build this ourselves since we have hundreds/thousands of developers?”

5. Lots of opportunities remain for software

Deployment of cloud applications is still relatively low but growing quickly.

“Rogue” usage of cloud applications is a real issue in enterprises.

Rising importance of the network between the end-user application and the enterprise website, and how important it is to performance.

High-end consumer websites are pioneering new applications and the new technologies ahead of everyone else (Facebook, Google, Netflix). Pay attention to what they do.

There is still a dearth of compelling enterprise mobile applications.

As I’ve written before, Internet infrastructure changes every five to seven years, creating new challenges and new opportunities, which give rise to new companies. All CIOs with whom I discuss software and SaaS have budgets for products which solve these new problems.

About Alex

I was trained as an engineer, paid for college by writing code, and have been backing technology startups since 1993. My partners and I founded Ridge Ventures, focusing on investing in SaaS and infrastructure solutions for enterprise companies.
More on my bio here.